Jake and I lived in the same apartment house and often met at the pool. He was manly and muscular so I didn’t think anything about his looks at my slim, girlish figure or teasing compliments that I would make a pretty girl. Hearing I was out of work, he invited me for a weekend to a friend’s mountain cabin before I started hunting for a job, and I accepted.

The area was isolated, and the quiet was a nice change. That night we played strip-poker (as I couldn’t afford to lose any money), and I was soon down to my briefs while Jake had only lost his shoes and socks. When I lost again, he offered me another chance: all of his clothes against tying me up naked. Having been tied up often in my childhood games, I didn’t mind it so I took the bed—and lost. I was tied on my bed with yards of clothesline and given thirty minutes to get free or pay a penalty. I failed, and the penalty was to put on the “Little Orphan Annie” costume supposedly left over from a costume party by a girlfriend.

Blushing as red as the curly wig, I shaved my sparse body hair, then slipped on the ruffled panties, training bra, short red dress with white Peter Pan collar and black Mary Jane shoes, all of which surprisingly fit me. There were other dresses, wigs, etc., in the closet and a purse with make-up. Going along with the penalty; I put on the light make-up and pink lipstick, and spent the next few hours tied up like “Annie” often was in the comics. Then I slept tied up in a frilly baby doll and new wig.

In the morning I was shocked to learn Jake had burned my clothes and, showing me copies of your magazine and Transvestite and Transformation catalogs, he said I was to be his sissy bondage sex slave. The cabin was his own, and he’d ordered the frilly and ruffled clothing, wigs, Mary Jane shoes, and feminizing pills and creams for me. My only job would be cleaning, cooking and sexually pleasing him. When I refused he strung me up by my wrists to the closet door and whipped me with a thick belt until I fainted. I woke to find I was cloth-gagged and hog-tied in the closet, still in my blonde Dutch boy wig and frilly nightie.

Hours later Jake returned and said he’d cleaned out my apartment and this cabin was my new home. For over a week I was kept in the closet, eating tied in a ball and being ass-fucked like that, besides sucking his cock repeatedly. Finally I had no choice but to agree to everything.

Though we were in a remote area Jake still kept me tied, especially when he was away, and the many ropes and positions were very ingenious; I’d never known there were so many ways to bind someone. I used the pills and creams and wore ruffled panties, training bra, corset (to slim my waist and give my hips and butt a rounder, girlish appearance) short dresses or longer, frilly ones (often with petticoats), anklet socks, panty hose, or bare legs and no socks, and different colored Mary Janes, and wigs while growing my own long hair and doing house work in cuffs and chains. I obediently used the pills and creams, and practiced acting like a sissy, including speaking in a sexy, breathy Marilyn Monroe style. Often I was thrown over Jake’s lap, folded arms tied behind me, and spanked by hand, belt or hairbrush on my pantied or else naked ass, then stood, gagged and bound hand and foot, in a corner for hours.

Soon I noticed my breasts filled the training bra and my small cock had shrunk. Locked in a sissy dress and leather wrist and ankle cuffs and chains, I tried to escape but became lost in the woods and was caught. Tautly spread-eagled between two trees, I was lashed with a switch and folded belt, then ass-fucked. Back in the cabin, I was stripped to ruffled panties and training bra, then tied in the closet and made to suck his prick, letting him repeatedly cum in my mouth, face and over my body. Also gagged, I was kept in there two weeks and beaten and sexually abused every few hours. Properly cowed, I begged Jake’s forgiveness.

Locked in a FL4A Frenum Chastity from your catalog, I became a perfect “little sissy lady” and modeled frilly dresses, petticoats, ruffled undies, baby dolls, and “play” clothes for him. I became skilled at blow-jobs and masturbating Jake with my hands tied in front or back. Finally my tiny penis was permanently locked in a FL2C Frenum, denying me sex, and my breasts had slightly larger implants.

When Jake has a male friend over I am mouth and ass fucked at once while tied in my sissy clothes. I always please his friends, who love binding, spanking and fucking me to exhaustion!